Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis
Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis
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DOI：
10.1021/ja0565368
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发表时间：
2006-03-22
影响因子：
15
通讯作者：
Seeberger, PH
中科院分区：
文献类型：
--
作者：
Liu, XY;Stocker, BL;Seeberger, PH
磷脂酰肌醇甘露糖苷（PIM），一个关键类的抗原糖脂上发现的结核分枝杆菌细胞壁的全合成进行了说明。该合成策略依赖于四甘露糖苷1和假三糖2的[4 + 3]糖基化，这允许聚合进入磷脂酰肌醇二甘露糖苷（PIM 2）和六甘露糖苷（PIM 6）的聚糖骨架。基于铜催化的交叉偶联反应，实现了结核硬脂酸的一个短的实用合成。聚糖和脂质部分的结合导致天然PIM 2和PIM 6的首次全合成。
The total synthesis of phosphatidylinositol mannosides (PIMs), a key class of antigenic glycolipids found on the cell wall of Mycobacterium tuberculosis, is described. The synthetic strategy relied on a [4 + 3] glycosylation of tetramannoside 1 and pseudotrisaccharide2, which allowed for convergent access to the glycan backbone of the phosphatidylinositol dimannoside (PIM2) and hexamannoside (PIM6). A short practical synthesis of tuberculostearic acid was achieved based on a copper-catalyzed cross-coupling reaction. Union of the glycan and lipid parts resulted in the first total synthesis of native PIM2 and PIM6.